Tetrahydrofuran → 1-Cyclohexyl-5-[4-(4-hydroxy-1-methyl-4-piperidinyl)-2-methoxyphenyl]-3-methyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Temperature

-78 °C

In an atmosphere of argon, 0.95 ml of n-butyl lithium (1.59M/hexane solution, 1.51 mmol) was added dropwise at −78° C. to a 10 ml anhydrous tetrahydrofuran solution of 300 mg (0.72 mmol) of the compound obtained in Example 15. The mixture was stirred at −78° C. for 30 minutes, and then 133 μl (1.08 mmol) of 1-methyl-4-piperidone was added, followed by heating the mixture gradually to 0° C. over the course of 1 hour. Then, water was added to the reaction mixture, and then the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/1) to obtain 179 mg (55%) of the captioned compound.

1. temperatureby heating the mixture gradually to 0° C. over the course of 1 hour
2. extractionthe mixture was extracted with ethyl acetate
3. dry with materialThe extract was dried over anhydrous sodium sulfate
4. distillationthe solvent was distilled off under reduced pressure
5. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/1)

ORD record

ord-0dccdb9d2a3b42118bb24c3baa76b994

Source dataset

uspto-grants-2007_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07268128B2